Meet Pauline Estelle — An English Lady in Canada

| Jan 1, 2018
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Pauline Estelle

Of all the trans/CD sites I have come across on the net this one seems to be the most mature and realistic so I thought I may have something worth while to say.

I was born 28 September 1935. That is 4 years before the start of the Second World War. Growing up in England at that time was quite different to the growing up process of later years but one didn’t realize it of course. Food rationing controlled everyones lives and what they ate. My elderly Grand Father was a gardener and he was classified  as an agricultural worker, the result of that being an increase of 8 ounces of cheese on his monthly dairy rations. Also my mother kept chickens in our garden. To get chicken feed we had to give up our egg ration. Ultimately, when the chickens were killed, we had to give up our meat ration until all the chickens were eaten. This gives a little insight into the food situation during the  war. Believe me there was no obesity. The bombs didn’t help either.

So back to crossdressing. Labels are a problem. My wife calls me Bi-gendered. This seems to me quite sensible as we have an arrangement which gives her some of my male persona and me, in equal portions, my female persona. (Pauline cheats where she can.)

My first venture in to crossdressing was when I was about 12 years old. I had an opportunity to put on an open bottom girdle, stockings and a bra. I was quite tall for age so they fit quite well and provided all sorts of new sensations for a twelve year old.

After this experience I had only a couple of other minor opportunities to wear female clothing. Consequently, this was my last crossdressing activity for many many years.

In Britain at that time, wearing clothes of the opposite sex was against the law. This was also true of homosexuality. A gay male was given the option of going to jail or being chemically castrated. If one knows the story of Alan Turing one will understand fully. (The movie The Waiting Game covers this very well.)

So life went on. Naval training school, entered the British Royal Navy at 16, served a four year marine engineering apprenticeship, 10 years at sea as a marine engineer, left the navy in 1965 as a 30 year old. During which time I got married and my wife gave me three sons, and we then emigrated to Canada in 1968.

I spent the next 40 years working in heavy engineering inspection and quality assurance. which involved a great deal of travel and a couple of relocations. Crossdressing did not become part of my life during this time. I came from a broken home where physical and verbal violence occurred and I was determined that my children were not going to be exposed to a failed marriage at all. This was helped by the fact that I deeply loved my wife so I did everything I could to make sure the marriage lasted. I did a little dressing in the intimacy  of our bedroom which was treated as fun by both of us but it never became an issue.

My boys grew up and went away to school or developed careers for themselves and at the ripe old age of 66 I retired. My Wife and I then spent the next few years touring most of the U.S.A. by car. Dressing was beginning to become more of a factor in my life in as much as I would spend more time on my computer searching applicable websites and dressing when I could. (mostly lingerie under my male clothing. Unfortunately, and very sadly my wife died of cancer in August 2109, after 51 years of marriage.

After a very trying grieving period when my life seemed to be getting back to normal, I became free to dress at will. This decision raises all sorts of questions of right and wrong, but where ever the truth lies the impulse to dress over rode any principles which may be involved. Does one create one’s own guilt? It’s hard to judge.

So now the next phase of my life has begun.

I was blessed with a wardrobe full of clothes, most of which fit me. albeit they were a little stuffy one might say, but they served their purpose as a stop gap while I assembled my own wardrobe.

I joined a crossdressing group in Toronto and got involved in their activities. Monthly Pub Nights, dinners, and local activities such as the Spring Fling in Gananoque on the St. Lawrence river. Getting out and about beyond the group was difficult. Everyone knows that when you are out you are being continually stared at. At least that’s what one imagines. However, I made a couple of very good friends who essentially bullied me to go out in public. After that, thanks mainly to them, I gained more confidence until there was very little nervousness. Today thanks to many factors, I have very little trouble when out — until I open my mouth.

A little while after this I was introduced to a woman who was aware of my dressing and helped me a great deal to update my wardrobe with a more modern look. She worked in a boutique style dress shop which catered to the ‘mother of the bride’  so there was a lot of experience there. She also helped a lot with my makeup.

The CD group ran an annual gala where they crowned a Queen for the year. Guess what, I won it. Only because of my new friend and her ability to select the right clothing and make up. The fact that I won upset some of the older members.

I joined the board of the group and over the next few years; I took on the role of secretary, got involved in the website development  until I realized that I was out of my depth, then I took over the role of running the Pub Nights for two years. I enjoyed this a lot. We would have presenters for such things as makeup, wigs, how to glam up a plain dress, jewelry, and the piece-de-resistance — fashion shows by suppliers. After two years I felt that someone else should do it with fresh ideas.

I remained very good friends with the Gals I had hooked up with initially. We went to Province Town, First Event in Boston, and a small event in Ogonquit, Maine, Crossing the border dressed was never a problem; in fact the U.S. border guards were extremely good. Some of them very funny. I wish I could say the same going the other way. We go out to dinner with CDs or not and of course shopping and movies, and have get-togethers in our respective homes.

In costume as Mae West.

While this was going on I married my new girl friend three and a half years ago and this gave my life a fresh fillip as we are having so much fun. My wife loves my male side as much as my female persona, so I share both sides of me on allocated days, We were at a Mexican resort this fall where I dressed all the time. This was interesting. I felt I had to present myself in the best possible manner as I don’t think there have been many CDs, if any, at the resort before, and I had an obligation to everyone to create a good impression for the benefit of the ’T’ in LGBTQ. It seemed to work out quite well as I got a number of compliments.

I  think this brings me up-to-date and I don’t want to be any more boring than I already have. I have other things to say about my impressions of trans-genderism, My relationship with my wife and my children and the future. By-the-way, I must add my health is pretty good for my age which allows me to do a lot of ‘stuff’ which I would other wise be denied.

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Category: Transgender Body & Soul


About the Author ()

I was born in England in 1935 and spent fourteen years in British Navy starting in 1951. I married in 1958 and stayed that way for 51 years. My wife gave me 3 sons all now in their fifties, only one knows of my little pecadilo. Four grand children all in or completed University. I emigrated to Canada in 1968. Worked for the oil, gas and power industries until I retired at 66. My first wife died of cancer in 2009. I was introduced to Gail by a mutual friend and we have been together six years and married for three. Gail was aware of my crossdressing before we married and supports it wholeheartedly with some rules. I have to be Paul some of the time, which is fair. I am a Libra and I own it.

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